Winthrop Vacation Rentals

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Vacation Rentals in Winthrop

Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop
Cottage on Cobbosseecontee Lake. Dates available.
10.0 out of 10, Exceptional, (155)
"We spent a week at this beautiful home and had a wonderful time. We took our bass boat and were able to launch it right on the property and tie it which was really convenient! We went fishing off and on all week on this beautiful lake. There were loons everywhere! Their calls are just entrancing."
Cottage on Cobbosseecontee Lake. Dates available.
Dog Friendly Cabin Right On The Water!!!
Interior
Dog Friendly Cabin Right On The Water!!!
2.0 out of 10, (1)
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so steep I couldn't find an entrance to the lake, I finally found a foot wide muddy, slippery path which was 90 degrees straight up and down. I only took a few steps and realized I would break my neck if...
Dog Friendly Cabin Right On The Water!!!
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Fridge, microwave, oven, stovetop
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
9.8 out of 10, Exceptional, (24)
"Well kept with all the right amenities. Beautiful views."
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Lakefront Cottage - sleeps 6 - 2 baths
Property grounds
Lakefront Cottage - sleeps 6 - 2 baths
10.0 out of 10, Exceptional, (2)
"Great size, very clean. The posted pictures do not do this camp justice! Lots of upgrades and Beth is very responsive. Beautiful cove with little traffic. Sounds of loons day and night. Great bass fishing too! There is a wonderful dock but be sure to bring your own water toys. Great place for children with neighbors that encourage lots of kid play, exploring/adventuring, and boisterous fun."
Lakefront Cottage - sleeps 6 - 2 baths
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Fridge, microwave, stovetop, dishwasher
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
10.0 out of 10, Exceptional, (26)
"The property was as advertised! For a family with little kids, this was a great place to stay. David was helpful and very responsive!"
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
Exterior
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
9.8 out of 10, Exceptional, (23)
"This was an amazing experience and the vision that the owners have is amazing I highly recommend this place"
The price is CA $136
CA $222 total
includes taxes & fees
Oct 8 - Oct 9
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
Lakefront Hartford Cabin w/ Canoe & Boat Ramp
Exterior
Lakefront Hartford Cabin w/ Canoe & Boat Ramp
9.6 out of 10, Exceptional, (26)
"This was an exceptional value in a relaxing time away. The cabin has recently been remodeled. The views out the back are impressive. We watch the sunrise every morning. "
Lakefront Hartford Cabin w/ Canoe & Boat Ramp
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
8.0 out of 10, Very good, (14)
"Beautiful place. Loons, eagles, Ospreys, and good fishing. No A/C made a couple of days miserable when heat and humidity was in the mid-nineties. Many fans available, though. Would be more ethical to let people know before booking that tap water is not drinkable. Saying a kayak is available is a bit of a stretch (small plastic boat)."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Cozy Lake House on Cobbosseeconte Lake
Outdoor dining
Cozy Lake House on Cobbosseeconte Lake
10.0 out of 10, Exceptional, (46)
"Thoroughly enjoyed our stay and accommodations. "
The price is CA $543
CA $716 total
includes taxes & fees
Sep 23 - Sep 24
Cozy Lake House on Cobbosseeconte Lake
An Authentic Clean & Cozy Maine Homestay
Fridge, microwave, oven, stovetop
An Authentic Clean & Cozy Maine Homestay
10.0 out of 10, Exceptional, (52)
"Property just as described on web site, great for a home-base, no problems (except for bike performance). Master bed on 2nd floor, with bathroom on first - let those kids do the steps in the middle of the night! Needless to say, we used separate beds on the first floor. Otherwise, great accommodations."
The price is CA $174
CA $275 total
includes taxes & fees
Sep 30 - Oct 1
An Authentic Clean & Cozy Maine Homestay
Hartford Cottage w/Dock + Private BCH on Bear Pond
Property grounds
Hartford Cottage w/Dock + Private BCH on Bear Pond
8.4 out of 10, Very good, (25)
"The house is on a beautiful pond (which is more like a lake) with beautiful sunsets and atmosphere (especially the loons!). It is actually quite convenient to grocery stores and other businesses. We enjoyed the grill, canoe and firepit. The bed is very comfortable, and the bathroom is roomy with great water pressure and hot water. Great spaces to hang out inside and outside. Considering going again next summer."
Hartford Cottage w/Dock + Private BCH on Bear Pond
Sunset Chalet- Stylish Waterfront Gem
Fridge, microwave, stovetop, coffee/tea maker
Sunset Chalet- Stylish Waterfront Gem
10.0 out of 10, Exceptional, (21)
"The property was beautiful, the cottage was clean and inviting."
The price is CA $661
CA $1,233 total
includes taxes & fees
Sep 23 - Sep 24
Sunset Chalet- Stylish Waterfront Gem
Waterfront 2br/2ba cottage
Fridge, microwave, oven, stovetop
Waterfront 2br/2ba cottage
9.6 out of 10, Exceptional, (8)
"This was a nice quiet spot to relax with family. The stream is on the property, and Gardiner was a great location to make as the base for our adventures around Maine. The owners couldn’t have been nicer"
The price is CA $217
CA $556 total
includes taxes & fees
Sep 25 - Sep 26
Waterfront 2br/2ba cottage
Nature lovers Paradise your own island
Nature lovers Paradise your own island
9.8 out of 10, Exceptional, (64)
"I have visited this idyllic spot about 10-12 times, and each time I am reminded of why I love it so much: the feeling of isolation on your own private island, the company of the cheerful small birds, the magnificent osprey family in the tallest tree (their nest is a few feet from the cabin), the view down the lake from the porch and living area, the curtain of trees surrounding the cabin, the warm water for swimming, the calm quiet at night, and the parade of ducks and loons nearby. And I...
Nature lovers Paradise your own island
Get in touch with nature.
Exterior
Get in touch with nature.
10.0 out of 10, Exceptional, (20)
"Nice location, beautiful tent, quiet place among the forest. Great for a retreat"
The price is CA $136
CA $222 total
includes taxes & fees
Sep 23 - Sep 24
Get in touch with nature.
Rustic, lakefront fishing cabin on Webber Pond with sunset views - 2 dogs OK
TV, DVD player, books
Rustic, lakefront fishing cabin on Webber Pond with sunset views - 2 dogs OK
8.8 out of 10, Excellent, (6)
"Peaceful and relaxing. A few things would have been nice to know ahead of our trip. Difficult to get to the water to swim. Did not know when trash pick up was scheduled and had to remind owner that it was not picked up. All that being said - it was very enjoyable"
Rustic, lakefront fishing cabin on Webber Pond with sunset views - 2 dogs OK
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
Property grounds
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
10.0 out of 10, Exceptional, (3)
"Great time!"
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE
Smart TV, books
ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE
10.0 out of 10, Exceptional, (53)
"Many thoughtful details offered comfort, convenience and privacy. If we make it back to Bowdoinham, we would love to stay here again! "
ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE
Private and Calming Waterfront to the Rescue!
Property grounds
Private and Calming Waterfront to the Rescue!
9.8 out of 10, Exceptional, (71)
"My husband and I plus our adult son, our daughter, son-in-law and our two young grandsons stayed at the lake house the last two weeks of August. What a beautiful, peaceful place. We loved hearing the loons calling every evening. We enjoyed using the provided paddle boat and kayaks. The outside of the house could use a little updating, specifically the front door deck, but the inside was renovated recently and very clean. We had a small family reunion on the Sunday after we checked in. The...
Private and Calming Waterfront to the Rescue!
SkyView Treehouse- Luxury Waterfront Retreat
Interior
SkyView Treehouse- Luxury Waterfront Retreat
10.0 out of 10, Exceptional, (3)
"Absolutely stunning home and location. From all the little details in the house and the host always made sure we had everything we needed and that he was just a text away if we needed anything at all. We had use of the kayaks and I would definitely suggest that because the scenery is just beautiful. Feras and his family are great hosts and I highly recommend them. "
The price is CA $586
CA $1,140 total
includes taxes & fees
Sep 23 - Sep 24
SkyView Treehouse- Luxury Waterfront Retreat
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Winthrop you may be interested in

Dog Friendly Cabin Right On The Water!!!
Interior
Dog Friendly Cabin Right On The Water!!!
2.0 out of 10, (1)
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so steep I couldn't find an entrance to the lake, I finally found a foot wide muddy, slippery path which was 90 degrees straight up and down. I only took a few steps and realized I would break my neck if...
Dog Friendly Cabin Right On The Water!!!
Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop
Cottage on Cobbosseecontee Lake. Dates available.
10.0 out of 10, Exceptional, (155)
"We spent a week at this beautiful home and had a wonderful time. We took our bass boat and were able to launch it right on the property and tie it which was really convenient! We went fishing off and on all week on this beautiful lake. There were loons everywhere! Their calls are just entrancing."
Cottage on Cobbosseecontee Lake. Dates available.
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Fridge, microwave, oven, stovetop
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
9.8 out of 10, Exceptional, (24)
"Well kept with all the right amenities. Beautiful views."
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals close to popular sights in Winthrop, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Winthrop?

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak: Visitors like this Winthrop vacation home rental. It is located on a lake and has a fireplace, a patio, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winthrop?

Expedia has 13 vacation rentals for your stay in Winthrop.

What can I see and do in Winthrop?

Cobbosseecontee Lake and Annabessacook Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Maranacook Lake and Wilson Pond are other places worth a visit.

What are vacation rentals like in Winthrop?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Winthrop. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.